4-Nitrobenzyl chloride

HCID 7482CAS 100-14-1

Basic information

Standard SMILES
O=[N+]([O-])c1ccc(CCl)cc1
InChIKey
KGCNHWXDPDPSBV-UHFFFAOYSA-N
Molecular formula
C7H6ClNO2
Average molar mass
171.58 g/mol
Monoisotopic mass
171.00870611

Overview

Benzene, 1-(chloromethyl)-4-nitro- is a solid. (EPA, 1998)

Names & identifiers

Preferred name
4-Nitrobenzyl chloride
IUPAC
1-(chloromethyl)-4-nitrobenzene
English name
4-Nitrobenzyl chloride
Molecular formula
C7H6ClNO2
Molecular weight
171.58

Names & synonyms

4-Nitrobenzyl chloride100-14-11-(Chloromethyl)-4-nitrobenzenep-Nitrobenzyl chlorideBenzene, 1-(chloromethyl)-4-nitro-alpha-Chloro-p-nitrotoluenep-(Chloromethyl)nitrobenzene4-(Chloromethyl)nitrobenzeneDTXSID40257454-nitrophenylmethyl chlorideToluene, alpha-chloro-p-nitro-3BLD9LVT3X
Show more names
p-nitrochlorideAKOS BBS-00003951NitrochlorobenzylNitrobenzylchlorideNitrobenzyl chloridà-chloro-4-nitrotolueneα-Chloro-4-nitrotoluene
BENZENE, 1-CHLOROMETHYL-4-NITRO-NSC-9803DTXCID105745CHEBI:87406para-nitrobenzyl chlorideRefChem:525941202-822-7alpha-Chloro-4-nitrotoluene

Database identifiers

CAS
100-14-1
PubChem CID
7482
DTXSID
DTXSID4025745
ChEMBL
CHEMBL176410
ChEBI
CHEBI:87406
UNII
3BLD9LVT3X
EC Number
202-822-7
Nikkaji
J4.978F

Properties

Computed structural properties

XLogP
2.5
Topological polar surface area
45.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
11

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Nitros, Aromatic
SpringerMaterials PropertiesDensity
Density1.5647 (NTP, 1992) - Denser than water; will sink
Color/FormPlates or needles from alcohol
Solubility · 2 items

Insoluble (NTP, 1992)

Sol in alcohol, ether, acetone, benzene

Boiling Point230 °C @760 [mm Hg]

Physicochemical properties

Melting point
71 °C · 71 °C
Boiling point
112 °C · 112 °C (0.6 mmHg)
Density
1.3246 · 1.3246 (rough estimate)
refractive index
1.5647 · 1.5647 (estimate)
solubility
50 mg/mL, · chloroform: soluble50mg/mL, clear to very slightly hazy, faintly yellow
form
Crystalline Needles or Powder

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P321, P330, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

Hazard information

Regulatory Information4-Nitrobenzyl chloride: Does not have an individual approval but may be used under an appropriate group standard
DOT LabelCorrosive
Fire HazardsIncompatible with sodium hydroxide. (EPA, 1998)
Health HazardsPoisonous if swallowed or dust is inhaled. (EPA, 1998)
Hazards SummaryPoisonous by ingestion and inhalation; [CAMEO] Corrosive; Causes burns; A lachrymator; May cause pneumonitis and pulmonary edema after inhalation of high concentrations; [MSDSonline]
Reactive GroupHalogenated Organic Compounds

Safety & protection

Fire FightingKeep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing.
First Aid · 1 item

Signs and Symptoms of Acute Benzene, 1-(Chloromethyl)-4-Nitro-Exposure: Signs and symptoms of acute exposure to benzene, 1-(chloromethyl)-4-nitro- may be severe and include cyanosis (blue tint to the skin and mucous membranes), tachycardia (rapid heart rate), hypotension (low blood pressure), and cardiac arrhythmias. Respiratory depression and respiratory failure may also occur. Headache, lethargy, weakness, vertigo (dizziness), severe depression, and coma may be noted. GI symptoms include nausea and vomiting. Urine and vomitus may have the odor of bitter almonds.

Nonfire Spill ResponseKeep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. If water pollution occurs, notify appropriate authorities. Do not touch spilled material; stop leak if you can do so without risk.
Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Protective Action Criteria (PAC) · 3 items

0.18 [mg/m3]

2.0 [mg/m3]

12 [mg/m3]

Personal Protective Equipment (PPE) · 1 item

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.
Non-Human Toxicity Excerpts · 2 items

The mutagenicity of 24 benzyl derivatives, containing a variety of substituents & leaving groups, were assayed in strain TA100 using Ames plate incorporation assay. P-nitrobenzyl chloride (12000 revertants/umole) was mutagenic. It was also mutagenic in strain TA98 (700 revertants/umole), but not in strain TA98NR (a strain deficient in nitro reducatase activity). This study suggests that nitrobenzyl derivatives were mutagenic due to nitro reductive metabolism.

Benzyl chloride, benzyl bromide, p-methylbenzyl chloride, & p-nitrobenzyl chloride were used to study chem reactivity with 4-(p-nitrobenzyl)pyridine & guanosine in vitro, in relation to mutagenic potency in Salmonella typhimurium & sister chromatid exchange (SCE) induction in CHO cells. Benzyl bromide was most reactive, followed by p-methylbenzyl chloride, benzyl chloride, & p-nitrobenzyl chloride. The order of mutagenicity was p-nitrobenzyl chloride much greater than benzyl bromide which was greater than benzyl chloride which was similar or equal to p-methylbenzyl chloride. They caused base-pair mutations only. The order of SCE-inducing ability decreased as follows: benzyl bromide greater than benzyl chloride which was similar or equal to p-nitrobenzyl chloride which was similar or equal to p-methylbenzyl chloride. The high mutagenicity of p-nitrobenzyl chloride in bacteria may be due to reactions other than direct aralkylation.

Toxicity DataLCLo (rat) = 280 mg/m3/4h

Regulatory information

CERCLA Reportable Quantities · 1 item

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Benzene, 1-(chloromethyl)-4-nitro- is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 500/10,000 lbs.

Safety data

F
4.8-19-21
PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
tsca
TSCA listed
rtecs
XS9093000
ridadr
UN 3261 8/PG 2

Chemistry & industry

Pharmacology

Metabolism/Metabolites4-nitrobenzyl chloride has known human metabolites that include 4-nitrobenzyl-glutathione and S-(4-Nitrobenzyl)glutathione.

Uses & manufacturing

U.S. Exports(1987) No Data
U.S. Imports(1987) No Data
U.S. Production(1987) No Data
General Manufacturing InformationBenzene, 1-(chloromethyl)-4-nitro-: ACTIVE
Applications · 3 items

DescriptionBenzene, 1-(chloromethyl)-4-nitro- is a crystalline solid. Molecular weight= 171.58; Freezing/Meltingpoint =71℃. Slightly soluble in water; slow reaction.

Uses4-Nitrobenzyl chloride was used to prepare unsymmetrically N,N′-bis(substituted) 4,13-diaza-18-crown-6-ether derivatives.

General DescriptionSolid.

Suppliers21 total

Xinxiang Juyuan Biological Technology Co., Ltd.+8615637360870 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]
北京京土恒盛化工科技有限公司00-13911456598 13911456598 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]

Additional notes

DefinitionChEBI: A C-nitro compound that is nitrobenzene in which the hydrogen at position 4 is replaced by a chloromethyl group.

Related reactions

145 records

Linked notes

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